CPP

IIT-JEE
CPP-1 Class – XI
GENERAL ORGANIC CHEMISTRY
1. The following Lewis structures A through L are isomeric (molecular formula CN2H2). This question requires you to
locate formal charges and electron deficient atoms (atoms that have not achieved a valence shell electron octet
through covalent sharing).

(a) Which structures have no charged atoms? ...............

(b) Which have at least one nitrogen atom with a (+)charge? ..
(c) Which have at least one nitrogen atom with a (–)charge? ...
(d) Which have at least one carbon atom with a (+)charge? .....
(e) Which have at least one carbon atom with a (–)charge? ......
(f) Which have electron deficient heavy atoms (N or C)? ......

2. Fill in the blanks for each of the following compounds :

For A to F. Find out the following (separately)

(a) Number of sp3 carbons: ..............
(b) Number of sp2 carbons: ...............
(c) Number of sp carbons: ................
(d) Number of carbon-carbon σ-bonds: .......
(e) Number of π-bonds to carbon: .............

FIITJEE 1
3. Discuss the basic strength of two nitrogens in benzimidazole.
1
N

N2
H
Benzimidazole

4. In the following structure which is better site of protonation and why-oxygen or nitrogen?
3 2
4 1 H+
O N

5. Compare the C–N bond length in the following species :

H2N H2N H2N

(i) (ii) (iii)

O

6. Rank the following in increasing order of basic strength explaining reason for your choice :
H H
N– Li+ N N
(i) (ii) (iii)

7. Answer the following

(i) Which of the indicating H is abstracted rapidly as a radical and why?
Ph Hc

Hb
Ha

FIITJEE 2
 (ii) One of the indicated proton, Ha or Hb, is approximately 1030 times more acidic than other. Which is more acidic
and why ?
H H
Ha
Hb

8. In each of the following pairs of ions which ion is more stable.

 
(a) (i) C 6 H5  C H 2 and (ii) CH 2  CH  C H 2

 
(b) (i) CH3  C H 2 and (ii) CH 2  C H

(c) (i) CH2 (ii) CH2

and

(d) (i) CH3 – CH– CH3 (ii) CH3 – N– CH3

and
CH3–C–CH3 CH3–C–CH3
9. Which of the following groups cannot participate in resonance with other suitable group
  
(a) –COOH (b) –COO– (c) –COCl (d)  N H 3 (e)  C H 2 (f)  C H 2

CH2 = N –
(g)
CH3

10. Which of the following group can participate with the other suitable group in resonance

H2

(a) CH 2  O (b) CH 2  CH 2 (c) –CH 2 – CH 2 (d) C

CH = CH 
(e) (f) –BH2 (g)  P Ph 3

11. In which of the following lone-pair indicated is involved in resonance :

(a) (b) (c) (d)

N
N N N
H
H
(e) CH 2  CH  CH2  
(f) CH 2  CH  CH  N H

12. Which of the following groups can donate as well as withdraw a pair of electron in resonance depending upon
situation
(a) –NO2 (b) –NO (c) CH = CH2 (d) –CHO
(e) –NH2 (f) –N= NH

* * * * *

FIITJEE 3
 ANSWERS
1. (a) B, C, G; (b) A, D, E, F, H, I, J; (c) A, D, E, K, L; (d) K, L ; (e) F, H, I, J ; (f) B, I, K, L.

2. A – (a-6) (b-4) (c-0) (d-10) (e-2) B – (a-0) (b-7) (c-2) (d-9) (e-6)
C – (a-5) (b-1) (c-0) (d-5) (e-1) D – (a-1) (b-3) (c-1) (d-3) (e-4)
E – (a-2) (b-3) (c-0) (d-2) (e-2) F – (a-10) (b-0) (c-0) (d-10) (e-0)

3. 1 is more basic than 2

4. 4

5. (i) < (ii) < (iii)

6. (i) > (ii) > (iii)

7. (i) HC Reason : Homolytic bond dissociation energy is inversely proportional to free radical stability.
(ii) Ha Reason : The resultant conjugate base is aromatic.

8. (a-ii) (b-i) (c-ii) (d-ii) 9. d 10. a, e, f, g 11. b, d, e

12. b, c, f

FIITJEE 4
 CPP
IIT-JEE
CPP-2 Class – XI
GENERAL ORGANIC CHEMISTRY
1. In which of the following pairs, indicated bond has greater strength :
(a) (i) CH3  CH 2  Br and (ii) CH3  CH 2  Cl (b) (i) CH3  CH  CH  Br and (ii) CH3  C  CH 3
    |
Br
O

C

(c) (i) H3C Cl and (ii) CH3  CH 2  Cl (d) (i) CH 2  CH  CH  CH 2 and
 

(ii) CH 2  CH 2  CH 2 – CH 3


(e) (i) CH 2  CH  CH  CH 2 and (ii) CH 2  CH  NO2 (f) (i) CH3 (ii)

 
and
C2H5 C2H5

2. In which of the following pairs, indicated bond having less bond dissociation energy :

(a) (i) and (ii) CH 2 CH 2 (b) (i) CH3  C  CH and (ii) HC  CH

  

(c) (i) HC=H2C CH = CH2 (ii) HC=H2C CH = CH2

 and
C C

CH2 CH2

(d) (i) O (ii) O (e) (i) O O

 and  (ii)
C C and
C C
NH2 NH2 H3C NH2 Cl


Cl H3C Cl

3. Which of the following has longest C – O bond :

O (b) O (c) O (d) O

(a)
CH2

4. CH3 O  CH  CH  NO 2 I
CH 2  CH  NO2 II
CH2 = CH –Cl III
CH2 = CH2 IV
Which of the following is the correct order of C–C bond lengths among these compounds :
(a) I > II > III > IV (b) IV> III > II > I (c) I > III > II > IV (d) II > III> I > IV

FIITJEE 5
5. Compare the C–N bond lengths for 1, 3 & 5 carbon atoms :
NO2
5

1 3
O2N NO2
Br

6. Number the following compounds in order of increasing acidity of indicated proton giving mechanistic reasoning

(a) O –H (b) CH2–H (c) CH2–CH2–H (d) OH

7. From the following pair, select the stronger acid providing clear reasoning

(a) (i) (ii) (b) (i) NH3Cl (ii) NH3Cl

NO2 COOH or COOH or

8.

9.

10. From which compound Ag+ can remove the I– at a faster rate ?

FIITJEE 6
 (b & c) Which of the following reactions goes to farther extent ?

11.

* * * * *

ANSWERS

1. (a-ii) (b-i) (c-i) (d-i) (e-ii) (f-ii) 2. (a-i) (b-i) (c-ii) (d-i) (e-i)

3. b 4. a

5. Cl – N and C3– N bonds are same length but longer than C5-N bond

6. (a) > (d) > (b) > (c) 7. (a-i) (b-i)

8. 36.8 Kcal

FIITJEE 7
 CPP
IIT-JEE
CPP-3 Class – XI
GENERAL ORGANIC CHEMISTRY

1. Arrange the acidic strength of following hydrogens in the decreasing order.

H H
a c
H O
b

(A) c > b > a (B) a > b > c (C) a > c > b (D) b > a > c

2. O
a
b CH3
H3 C Oc

Compare the bond lengths a,b, and c.

(A) c > b > a (B) c > a > b (C) a > c > b (D) b > a > c

3. Compare the basic strength of the following bases.

NO 2

N N
(i) (ii) NH2
(iii)
(A) i > iii > ii (B) ii > iii > i (C) i > ii > iii (D) iii > ii > i

4. Compare the acidic strength of the following hydrocarbons :

(i) (ii) (iii)

(A) iii > ii > i (B) i > ii > iii (C) i > iii > ii (D) ii > i > iii

5. Compare the acidic strength of the labelled hydrogens a d

HO COOH
(A) a > c > d > b
(B) c > a > d > b
(C) d > a > b > c
(D) d > a > c > b Hc
HO
b

FIITJEE 8
6. Arrange the following compounds in the increasing order of acidic strength.
O O O O O

O OCH3
O
O O
(i) (ii) (iii)
(iv)
(A) i > iv > iii > ii (B) i > iv > ii > iii (C) iv > i > ii > iii (D) iv > i > iii > ii

7. Compare the acidic strength of the labelled hydrogens. O O Hc

(A) a > b > c (B) b > a > c H
(C) b > a > c (D) a > c > b a O
Hb
8. Decreasing order of acidic strength of following CN
compounds is
(A) iii > i > ii (B) i > ii > iii
(C) i > iii > ii (D) ii > i > iii
(i) (ii) (iii)

+
9. Compare the stability of the following carbocations. CH 2
(A) iii > i > ii (B) i > ii > iii

(C) i > iii > ii (D) ii > i > iii  CH 2

(i) (ii) (iii)

10. Compare the acidic strength of the following compounds :
O O O O O

O
(i) (ii) (iii)

(A) iii > i > ii (B) i > ii > iii (C) i > iii > ii (D) ii > i > iii
11. Compare the stability of the following carbocations ?
+
+
+
+
(i) (ii) (iii) (iv)
(A) i > iv > iii > ii (B) i > iv > ii > iii (C) i > ii > iii > iv (D) iii > i > ii > iv
12. The following structures are resonance contributors for a reactive intermediate formed during ozonolysis of alkenes.
Identify the most energetically favorable and the least favorable contributors?

(A) III is most favorable & II is least favorable (B) I is most favorable & IV is least favorable
(C) II is most favorable & IV is least favorable (D) I is most favorable & II is least favorable
ANSWER KEY
1. (C) 2. (A) 3. (C) 4. (C) 5. (C) 6. (D) 7. (B) 8. (A)
9. (D) 10. (A) 11. (D) 12. (B)

FIITJEE 9
 CPP
IIT-JEE
CPP-4 Class – XI
GENERAL ORGANIC CHEMISTRY
1. What formal charges are present in the molecule C6H5C≡N-O?
(all heavy atoms have a valence shell octet, and C6H5- is a phenyl group)
(A) N is -1 and C is +1 (B) N is +1 and C is -1 (C) O is -1 and C is +1 (D) O is -1 and N is +1

2. The structural formula for vitamin C is shown below of the four hydroxyl groups,
identified by shaded circles, which is most acidic?

(A) 1
(B) 2
(C) 3
(D) 4

3. Which of the following structures is not a resonance contributor to the hybrid defined by the other three?

4. Compare the basic strength of the following compounds.

N
1. 2. 3. 4.
N
N N N
N
H H H

(A) 2 > 3 > 4 > 1 (B) 3 > 2 > 4 > 1 (C) 3 > 4 > 2 > 1 (D) 2 > 4 > 3 > 1

5. Which of the following is not a resonating structure of the others ?


O
O O O

 
1) 2) 3) 4)


6.

a) b) c)

Compare the ease of rotation of indicated bonds in the above compounds

(A) a > b > c (B) b > a > c (C) c > b > a (D) a > c > b

FIITJEE 10
7. Which of the following acids would have a stronger conjugate base ?
A) H 2S or H 2O C) CH 3C  CH or CH3CH=CH 2
1 2 5 6

O O

B) NH or NH

O
4
(A) 2, 4, 63 (B) 1, 3, 5 (C) 2, 3, 5 (D) 1, 3, 6

8. Which of the following has the highest dipole moment ?

(A) naphthalene (B) benzene (C) azulene (D) anthracene

9. Which of the following is the strongest acid ?

O O O
1) 2) 3) CH2(CO2Et) 2 4) CH3COCH2COOC2H5
O
10. Resonance is not observed in
(A) CH 2 =CHNH3+ (B) CH 2 =CH-CH=NH 2 + (C) CH 2 =CHOH (D) CH 2 =CHCl

11. Which of the following isomeric hydrocarbons is most acidic?

12. Which of the following compounds has the highest PKa value ?
+
H2 H2
NH2 NH3 N N
+ + +
1 H2 N 2 HN 3 4
NH2 NH2

ANSWER KEY
1. (B) 2. (C) 3. (A) 4. (B) 5. (A) 6. (B) 7. (A) 8. (C)
9. (D) 10. (A) 11. (B) 12. (A)

* * * * *

FIITJEE 11